Islamorada Holidays
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Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Matecumbe
5 out of top 10 points of interest in this area
If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Florida Keys Brewing Co. are top sights worth seeing.
Top hotels in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 4.965.587 ₫ per night from 28 Jan to 29 Jan
4.965.587 ₫
7.063.715 ₫ total
28 Jan - 29 Jan
includes taxes & fees
9.2/10 Wonderful! (1,624 reviews)
Clean, gorgeous view, amazing free breakfast, loved the robes!
Reviewed on 10 Jan 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 7.791.809 ₫ per night from 21 Jan to 22 Jan
7.791.809 ₫
10.509.321 ₫ total
21 Jan - 22 Jan
includes taxes & fees
8.8/10 Excellent! (124 reviews)
Amazing place - so much variety
Reviewed on 6 Jan 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 7.123.339 ₫ per night from 29 Jan to 30 Jan
7.123.339 ₫
9.934.589 ₫ total
29 Jan - 30 Jan
includes taxes & fees
9.2/10 Wonderful! (1,287 reviews)
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.
Reviewed on 8 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Anne's Beach
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
Founders Park
Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander through the seaside and beautiful beaches in this family-friendly area.
